Takes

Coach K will win 'Retirement of the Year' multiple times because he wants a year-long 'suck my dick' tour

I'm going to say coach K is going to win it this year. And he's going to win next year when he actually does retire because coach K has said that he's going to retire, but he needs everyone to suck his dick for an entire year before he actually retired. He could probably be talked into coming back... then he could have a dynasty of retirement.